1-Amino, 3-substitutedphenylcyclopentanecarboxylates are important intermediates for the preparation of a useful class of biologically-active molecules. The processes disclosed in the art for the preparation of these compounds do not address the isolation of stereoisomers with enriched diastereomeric and/or enantiomeric excess. As such there is a need for the development of a process that addresses the isolation of material with diastereomeric and enantiomeric enrichment.
In contrast to previously known processes the present invention discloses an effective method for the preparation and isolation of (1R,3R)-methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate, (1R,3S)-methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate, (1S,3S)-methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate, (1S,3R)-methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate, (1R,3R)-1-amino-3-(4-methoxyphenyl)cyclopentanecarboxylate, (1S,3S)-1-amino-3-(4-methoxyphenyl)cyclopentanecarboxylate which is high yielding and provides for enrichment in both diastereomeric and enantiomeric excess.
These compounds are intermediates in the synthesis of other compounds that possess pharmacological activity. In particular, these other compounds include but are not limited to S1P1 agonists such as those described in WO 2007089715 A2, WO 2006088944 A1 and other publications. S1P1 agonists are useful, e.g., in the treatment of inflammatory diseases and conditions, and in the treatment of other diseases and conditions.